The Ultimate 5-Day Maui Travel Itinerary

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Maui is one of my favorite places to go when I’m looking for a mix of adventure and relaxation. And no matter how long I spend there, it never feels long enough–but that’s ok; all the more reason to plan a return trip. This Maui travel itinerary will help you to maximize your time and hit the highlights without feeling rushed. And there’s leeway to add in another adventure or spend more time reading a book on the beach.

I give dinner suggestions for each day, but you can also check out my post about the best restaurants in Maui to give you more ideas. There are lots of great places, and many are suitable for the entire family.

Maui Travel Itinerary: Where to Stay on the Island

If you’re looking for a place to stay in Maui, I have lots of great family resort recommendations here. Wailea on the south side and Kaanapali on the west are two of the most popular resort areas—both offer beautiful beaches and great dining options.

Two of my favorite resorts on Maui are the Westin Maui Resort and the Grand Wailea Resort. But again, I offer a whole list of top options to stay in that will fit any budget here. You can’t go wrong with any of them.

🏝 Day 1: Arrival + Beach Time in Wailea or Kaanapali

Welcome to Maui! After picking up your rental car (yes, you’ll want one!), you might want to stop at Costco before heading to your resort or vacation rental. I know grocery shopping isn’t the most exciting thing for your Maui travel itinerary, but it’s right next to the airport. We love stocking up on some snacks and drinks for the week.

Take it easy today. Settle in, grab a mai tai, and head straight to the beach. Some great options:

• Kaanapali Beach (West Maui): Excellent for swimming and watching cliff divers at Black Rock.
• Wailea Beach (South Maui): Calmer waves, soft sand, and a gorgeous walking path.

Dinner idea:

• Merriman’s Kapalua for oceanfront views and fresh seafood.
• Monkeypod Kitchen in Wailea for laid-back vibes and local farm-to-table fare.

Try to get to bed early tonight, especially if you plan to do the sunrise at Haleakalā tomorrow.

🌄 Day 2: Sunrise at Haleakalā + Upcountry Wandering

Rise and shine—it’s time for a bucket list experience! I highly recommend doing this on the first morning of your trip for a couple of reasons. One, you won’t have adjusted to the time change yet, so it will likely feel a couple hours later when your alarm goes off. And secondly, you’ll still have many more days to sleep in and get you well rested after this early morning.

🚗 Sunrise at Haleakalā National Park

• Tip: Anyone entering the park between 3:00am and 7:00am will need a reservation, so book that in advance at Recreation.gov.
• Leave early (like…2:30 AM early) and bring warm layers—it gets really cold up there.
• Watching the sun rise above the clouds is seriously magical.

🍍 Explore Upcountry Maui

After the sunrise, head into Upcountry Maui, a beautiful, rural area with rolling hills and local farms.

• Ali’i Kula Lavender Farm – Stroll through peaceful lavender fields.
• Surfing Goat Dairy – Cute goats and tasty cheese samples.
• MauiWine – Wine tasting in a charming estate.

Because you had an early morning, you might want to spend the afternoon relaxing at the resort or a nearby beach.

Dinner: Take it easy back in your area. Consider grabbing poke bowls or enjoying a sunset dinner by the beach.

🌊 Day 3: Road to Hana Adventure – A must-do on any Maui travel itinerary

Ready for a full day of jaw-dropping scenery and hidden gems? The Road to Hana is an adventure on its own, but the number of beautiful waterfalls and stops along the way are surely icing on the cake.

🚗 Drive the Road to Hana

• Start early! This is an all-day excursion.
• Stop for banana bread along the way–there are lots of amazing stands in Paia, and it’s our favorite way to start the drive.
• Consider doing a tour if driving on this road makes you nervous.
• Download an audio tour or Shaka Guide for a great self-guided audio tour to do it on your own.
• Must-stop spots: (see my full list of the best stops on the Road to Hana here)
  • Twin Falls
  • Garden of Eden
  • Waianapanapa Black Sand Beach (reserve your timed entry)
  • Wailua Falls
  • Optional: Hike to Waimoku Falls in Haleakalā’s Kipahulu District

💤 Pro Tip: Consider staying overnight in Hana if you want to break up the drive, or plan to head back before dark.

Dinner: You’ll probably want something casual when you return. Food trucks or a quick meal from a local market will hit the spot.

🐠 Maui Travel Itinerary Day 4: Snorkeling + Lahaina Town

Time to explore underwater and soak up some island culture.

🐢 Snorkeling Tour

• Book a morning snorkel cruise to Molokini Crater and Turtle Town.
• You’ll see vibrant coral reefs, tropical fish, and maybe even sea turtles!

🛍 Explore Historic Lahaina (pre-fires, this was my suggested Maui travel itinerary, however much of Lahaina is still closed. Check for re-opening dates but still consider having dinner there to help support local businesses.

• Spend the afternoon in Lahaina Town (note: as of mid-2025, check for reopening updates following the 2023 wildfire recovery efforts).
• Walk along Front Street, grab some shaved ice, shop for souvenirs, and admire the famous banyan tree.
• Tip: Support local businesses and artisans as they rebuild and recover.

Because you won’t be able to spend as much time exploring Lahaina, you can use some of this day to explore more of Kihei after your snorkel tour. And if you aren’t staying on that side of the island, I suggest using this time to visit the Wailea beaches–there are some of the best family beaches in Wailea. Conversely, if you are staying in Wailea, you can use this time to visit the Kaanapali beaches and then grab dinner in Lahaina on your way back down.

🌴 Day 5: Chill Day – Choose Your Own Adventure

It’s your last full day in paradise, so make it count—your way. This day of the Maui travel itinerary is for you to use as you see fit. But I give several recommendations below.

🧘‍♀️ Relaxed options:

• Enjoy a spa treatment or beachfront massage.
• Lounge by the pool or beach with a good book.
• Try paddleboarding or kayaking from your hotel’s beach.

🏄‍♂️ Active options:

• Book a surf lesson in Kihei.
• Hike the Waihee Ridge Trail for incredible ocean views.
• Check out the Nakalele Blow Hole
• Snorkel in Honolua Bay
• Visit the Iao Valley State Park (reopened with improvements as of 2023).

Dinner: End your trip with a traditional luau—a fun and festive way to wrap up your Maui adventure.

• Old Lahaina Luau (book early!)
• Maui Nui Luau at the Sheraton Maui Resort
• Feast at Mokapu in Wailea (a bit more upscale)

✈️ Bonus Tips Before You Go

• Pack layers – It gets chilly at high elevations. Check out my Hawaii packing list to ensure you have everything you need.
• Sunscreen – Make sure it’s reef-safe!
• Reservations – Book key activities, restaurants, and parks in advance.
• Respect the land and local communities – Always leave places better than you found them.

Aloha and safe travels! Maui has a special kind of magic that lingers long after you’ve returned home. With this 5-day Maui travel itinerary, you’ll get the perfect taste of the island’s beauty, adventure, and aloha spirit.

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